


Working For The Man

by dastiel_gal (rock_chick)



Series: Secretary [3]
Category: Supernatural RPF
Genre: Alternate Universe - Gender Changes, F/M, Trans Female Character
Language: English
Status: Completed
Published: 2011-05-20
Updated: 2011-05-20
Packaged: 2017-10-24 06:51:05
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,670
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/260346
Author URL: https://archiveofourown.org/users/rock_chick/pseuds/dastiel_gal
Summary: <blockquote class="userstuff">
              <p>Jenny and Jared are right where Jeff wants them - which, today, means knickerless and under his thumb.  And he's fixing to push Jared all the way past his limits.  Jenny's only too happy to help him with that.  (Pre-op trans Jensen)</p>
            </blockquote>





	Working For The Man

**Author's Note:**

> Written for [](http://bittersweet-fic.livejournal.com/profile)[**bittersweet_fic**](http://bittersweet-fic.livejournal.com/) as part of the Five Acts kinky comment-fic meme [hosted here](http://toestastegood.livejournal.com/598881.html) by [](http://toestastegood.livejournal.com/profile)[**toestastegood**](http://toestastegood.livejournal.com/). Although it should be okay to read as a stand-alone, it follows on from my previous fics [Eat Your Heart Out, James Spader](http://dastiel-gal.livejournal.com/13736.html). and [Take A Memo, Miss Ackles](http://dastiel-gal.livejournal.com/20032.html), in what I'm gonna dub Secretary!verse. Oh, gawd, am I writing an actual 'verse, now? Somebody make me stop.

Jenny's in a fluster before she even gets to work. It's a bright, breezy day, and she keeps getting gusts of air in places she most definitely isn't used to. Not to mention, she feels hideously conspicuous; as if the whole world somehow _knows_ that she's bare under her skirt. Or like the whole world knows what's _under_ her skirt. It's been years since she worried about passing, but this is making her feel like everybody's looking at her. When Katie on reception comments on her flushed face, she just about dies on the spot, but manages to stutter something about the wind being bad for her complexion.

Jeff and Jared are both in a breakfast meeting first thing, so she has time to collect herself; and when they get out it's action stations to meet their deadline on this week's Ridiculously Urgent Report. They're too busy to breathe until it's finally done mid-afternoon, and the courier has gone off to their client with the package. She's almost completely forgotten, right up until Jeff calls switchboard and tells them to hold calls for the three of them, "internal meeting, not to be disturbed", and suddenly she's hot all over and, _Christ_ , getting hard under her skirt. She should think herself lucky it didn't happen earlier, somewhere even less appropriate, like on the train; but she's quite mortified enough to have her wayward cock trying to poke a hole in her skirt in the middle of Jeff's office. Even when she knows Jeff is a kinky fucker who will get off on it.

She hears Jeff lock the door and draw the blinds, then he snaps "Line up!", and she and Jared scramble to stand side by side in front of his desk. She sneaks a peek at Jared, and he looks as flushed as she feels ... and as hard.

"Did you both dress as I requested?" rumbles Jeff, leaning against his desk and fixing them with a piercing look. They both nod furiously. "Show me."

Jenny's reaching for her hem on the instant; she's played games like this before, and she knows her role. Jared's new to it, and he hesitates, hands hovering, until Jeff barks his name and he gulps audibly and fumbles with his fly. Jenny works her skirt up, inch by inch, teasing Jeff even as she complies with his orders. Jeff nods approvingly when they're both exposed, proving they'd left off their underwear as instructed.

"Good. Now, Jared, Jenny gave you an amazing blowjob yesterday. I think you should return the favour, don't you?"

Jenny's overwhelmed by conflicting emotions. On the one hand, the idea of Jared's mouth on her sends lust slamming through her body, she wants it like she wants to breathe; but she knows he's never done it before. Hell, the guy was straight as they come until he fell for Jenny. Then they got into these power games with Jeff, and Jay'd been so wound up by the time he'd found out about Jenny's cross-dressing that he'd just gone with it anyway. But when it comes to cock-smoking, there's a big difference between taking and giving, and she's not sure he's into her enough to put aside everything he thought he knew about his sexuality.

Jared's stuttering and trembling, red-faced and shaking his head. She thinks he's gonna haul his pants up and bolt for the door, and apparently Jeff's concerned about that too. He steps forward and takes firm hold of Jared's shoulders, grounding him.

"Listen, kid, nobody's gonna make you do jack shit. If you want out, the door's right behind you, just say the word. We're not gonna judge you if you go... and we're not gonna judge you if you stay. But think about it, Jared. You've been building up to this for months, dying to make a move, wanting to touch Jenny, be with her. Was that just about her body, or was it about _her_?"

Jared's head jerks up at that, a scowl on his face. "That's not fair, of course it wasn't just about her body! I really like Jenny! I've just... never... and I don't know _how_."

The thought that he might be willing to do it makes Jenny dizzy with want. She bumps shoulders with him and flashes him a hopeful grin. "It always feels weird the first time, Jay. Just... think about what you like to have done to you, and start from... oh." She's just remembered exactly _how_ Jared likes his blowjobs, and just, no. Not the first time, probably not even the tenth. "Um... actually, how about you just put the tip in your mouth, and use your hand on the rest?"

Thankfully, that's got Jared laughing and meeting her eye, and she gives him her most flirtatious look, peeping up at him between her lashes and biting one side of her bottom lip the way he Just. Can't. Resist. There's a blowjob on the line, after all; she's giving this one all her feminine wiles.

He stops laughing and she can practically see him gathering his courage. He slides down to the floor, and fuck, Jared on his knees for her is so hot it makes her cock twitch. He stops there though, staring fixedly at her shirt buttons, frozen and panicked; unable to make himself take the next step, until Jeff steps in to talk him through.

"Look up at her, Jared - yeah, right in the eye, that's good. Now, put your hand on her. You've done this bit before, kid, it's no biggie. Give it a little stroke, nice and gentle, yeah, keep going." Jeff has to clear his throat before he can continue, so Jenny doesn't need to look at him to know he's enjoying the view. She hears a zipper, and the rustle of fabric, and bites back a snigger. Good subs do not laugh at their doms mid-scene, even when they're being hilariously predictable kinky voyeurs.

Then Jeff's telling Jared to kiss the tip of her cock, and all desire to laugh evaporates in a moment of desperate need, followed by a jolt of heat when his lips touch her. She gasps, suddenly wobbly-kneed. He's still staring up at her, eyes wide and expression faintly shocked as he apparently decides it's not as awful as he expected. His lips part and slide a tiny bit further around her, wet and warm and amazing.

She gasps his name, and his face instantly registers satisfaction, pride at turning her on. Oh, yeah, he's gonna be so into this once they get him past his mental block. She makes sure to keep giving him little moans as he kisses and mouths at her, just by way of encouragement - but knowing this is the first time he's ever done this is insanely hot, and it's crazy but she's never felt so much from so little before, so when his mouth slips forward to take her whole head in, the noises start coming out of her louder, and for real. His hand's still working her, and he's watching her reactions closely. When he pulls off and flicks his tongue all over the top part of her cock as it pops in and out of his huge fist, she starts losing it in earnest.

Her legs don't want to hold her up any more; she sways dangerously on her heels and is glad when Jeff comes up right behind her and leans her against his chest, one arm around her waist to hold her steady as he slides his cock into the cleft between her ass cheeks and starts rubbing off against her.

"Good lad, you're doing so well. Getting her so hot she can't hardly stand up on her own. Faster with your hand, now, and give her a proper suck."

Even though she's only a couple of inches into his mouth, she swears she can feel the vibration of his reflexive gulp at Jeff's command, and the thought of one day having her cock all the way down his throat and feeling him swallow against her length - well, it's nearly enough to get her off then and there, even before he starts sucking her messily. She can feel herself start to spiral upwards towards her climax.

"Jeff, I'm close."

"That's great, darlin'. Jared, your choice whether she comes in your mouth or on your face."

Jared goes bright red in two seconds flat and looks a bit panicky again, but then his face sets in determination and he slides his lips another inch down her shaft, sucking harder. She's stunned that he's doing this, something he'd never wanted before - maybe doesn't even particularly want now - for _her_ , and going all the way with it just to give her pleasure. That's hot enough to damn near kill a girl, and his next suck pulls her over into a hot wave of ecstasy. Jeff's hand clamps down over her mouth to stifle her cries as she rides it.

She's not really with it for a while; she's aware of Jeff still working his hips against her ass, and Jared has pulled off and smushed his face into her belly as he jerks himself wildly. She's feeling boneless and entirely lazy, so she just props herself between them and lets them get on with it. She can just about summon up enough energy to run her fingers through Jared's hair, holding his head against her and tugging lightly on his locks. That drags an interesting noise out of him, so she does it again a touch harder, then harder still, and Jared keens, gives a full-body shudder and comes all over her stockings.

Jeff follows him soon afterwards, grunting and spurting up the crack of her bare ass. And on her skirt. Much more of this and she's gonna make the pair of them contribute to her dry-cleaning bill. And her lingerie habit. Yeah. It's _totally_ a legitimate work-related expense claim.

"And just what are _you_ smirking about, Missy?"

Oops, busted.


End file.
